Enhanced activity or resistance of adenosine derivatives towards adenosine deaminase-catalyzed deamination: Influence of ribose modifications

Bioorg Med Chem Lett. 2009 May 15;19(10):2877-9. doi: 10.1016/j.bmcl.2009.03.084. Epub 2009 Mar 24.


The effect of the presence of the 1'-C-methyl group and 2',3'-O-substitution in the adenosine structure on ADA activity has been investigated by modeling studies. Results show that the 2'- and 3'-O- substituents are harbored in a quite large cavity of intermediate polarity, whereas the 1'-C-substituent clashes against Ala180 distorting the architecture of the catalytic centre. Globally, the study emphasizes the ability of ADA to transform a large set of 2',3'-O-substituted adenosine analogues as well as the opportunity to design 1'-C-substituted adenosine derivatives resistant to ADA-catalyzed deamination.

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis
  • Adenosine Deaminase / chemistry*
  • Adenosine Deaminase / metabolism
  • Catalysis
  • Computer Simulation
  • Deamination
  • Ribose / analogs & derivatives
  • Ribose / chemical synthesis*
  • Ribose / chemistry
  • Structure-Activity Relationship


  • Ribose
  • Adenosine Deaminase
  • Adenosine